John Greenwood: Adroit Multi-talented Patriot

Autobiography and Biography

March 22, 2022
by Louis Arthur Norton Also by this Author


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This historical chronical is about an unusual multifaceted patriot: a musician, soldier, privateer, author, and dentist.

On May 17, 1760, John Greenwood was born to Boston ivory artisan Isaac and Mary Greenwood. Before the lad turned thirteen years old, John was a witness to the so called “Boston Massacre” that killed eighteen-year-old Samuel Maverick, his roommate and apprentice in his father’s business. He also witnessed the Boston Tea Party as well as several colonial bureaucrats being tarred and feathered. “Nothing was talked about but war, liberty, or death; persons of all descriptions were embodying themselves into military companies.”[1]These momentous events and divisive sentiments greatly impacted Greenwood’s early life.

As a young man the sound of the fifes and drums that accompanied drilling British troops captured his imagination. Greenwood salvaged a discarded fife, repaired it and learned to play several tunes. Because of the local unrest that was brewing, he was sent to live with an uncle, a cabinetmaker, in Falmouth (now Portland), Maine. In May 1775, news of the battle at Lexington and Concord reached that distant northeastern Massachusetts province. Greenwood placed his fife in his backpack, strapped on a sword and set off on foot to Boston approximately 150 miles away. On a quiet Sunday when few people were about, he traveled “the country so thinly inhabited that I had to traverse, at times, woods seven miles in length, and I had never traveled before more than three or four miles by land into the country.”[2] Occasionally pausing in villages, the lad played some tunes on his fife at wayside taverns. Greenwood later recalled that patrons “used to ask me where I came from and where I was going to, and when I told them I was going to fight for my country, they were astonished such a little boy, and alone, should have such courage. Thus by the help of my fife I lived, as it were, on what is usually called free quarters nearly upon the entire route.”[3]

When Greenwood passed through Cambridge, near where the battle had recently raged at Breed’s and Bunker Hill, wounded men were being laid out on the town’s nearby common. “Everywhere the greatest terror and confusion seemed to prevail.” The road that led to the battlefield was clogged with wagons carrying the wounded or the bewildered struggling back to Cambridge on foot. With no plans and almost out of money, the sixteen-year old reached an army encampment at which he impressed some officers with his musical abilities. The diminutive teenager was then enlisted in the army with the assurance of what was equivalent of eight dollars a month to become a fifer, one of several hundred in the army.[4] Besides the aftermath of Bunker Hill, he saw service in the siege and evacuation of Boston, the attack on Montreal in Canada and several wilderness skirmishes with Indians and small British units. After serving twenty months but only being paid for six, he became disillusioned with military life. When Greenwood’s enlistment was up, he returned to Boston and worked as a fisherman for two years and became a competent sailor.[5]

With these mariner skills, Greenwood’s next venture was becoming a crewman on a privateer. If successful, this was an opportunity for significant financial reward. During the Revolutionary War privateering was castigated for draining off manpower and ammunitions from the Continental Navy and Army and privateer owners were accused of degrading American morals by offering men the opportunity to place profit over patriotism. Privateering, however, greatly affected British commerce providing an oblique source of strength that helped the rebels to persevere. Although not a decisive factor in the defeat of the British, the large privateer fleet was an important if controversial cog in the martial machinery of the Revolutionary War.

Now nineteen, Greenwood signed on as steward’s mate and midshipman on the Boston based privateer sloop Cumberland whose captain, John Manley, had recently won fame as the commander of the Lee, part of what became known as George Washington’s six cruiser fleet. The Marblehead seafarer had captured the British ship Nancy that was ladened with munitions, badly needed by the fledgling Continental Army. The letter of marque had a crew of 130 and eighteen cannons. Its mission was to cruise off the island of Barbados to intercept westbound West Indian British merchantmen. Before long Cumberland captured a ship that had been dismasted in a gale. On board were some British soldiers, assorted goods including clothing, and a cargo of wine. A mast was jury rigged, and the prize vessel set sail to Martinique. The next day Cumberland encountered the British frigate Pomona with 300 men and mounting thirty-six guns. The American privateer was at an obvious disadvantage. The frigate’s captain ordered Manley to “strike your damned rebel colors.”[6] Manley ordered the Massachusetts white pine tree flag lowered. With this small act, Greenwood’s first privateer venture ended as Cumberland was seized by the British warship within days of its leaving port.[7]

Pomona sent a longboat to retrieve the American crew and incarcerate them below decks. The resourceful Greenwood stuffed non-perishable food and clothing into a sack then jumped into the boat with the rest of the privateer’s crew. The British frigate’s crew, however, confiscated anything of value and placed the prisoners in the ship’s hold. After about three or four days, Pomona and her prize arrived at Barbados where the rebel crew was conducted to the local prison. The next day they were informed that they would be distributed through the fleet as impressed British sailors. Greenwood devised a scheme to avoid this unwelcomed conscription. Cumberland’s ship’s “doctor” had been allowed to take his medicine-chest with him so that he could treat any rebel in medical need. Greenwood asked the doctor for two emetics, then swallowed them. When the soldiers came to march the prisoners to the yard, Greenwood started to violently vomit. “I thought I should have thrown up my entrails and shall never forget how sick I was.”[8] A British officer decided he was too sick to be of use to the Royal Navy and left him behind. Greenwood obtained release as part of a prisoner exchange sometime later and was taken to Martinique where he found passage back to New England.

His next privateering venture was on board the ill-fated Tartar, a ship that founderedneared Port-au-Prince forcing Greenwood’s return to Martinique. There he signed on the small letter of marque brig General Lincoln with a crew of twenty-five and six cannons. Off the Delaware Capes, the Royal Navy sixth rate ship Iris easily captured the outgunned General Lincoln by firing only a few shots.[9] The captain of Iris, James Hawker, evacuated the privateer’s crew to take the brig as a prize, but the trophy ship was leaking badly. Hawker heard that Greenwood, who had lived with a cabinetmaker uncle in Maine, had developed some carpentry skills. Rather than being incarcerated in Iris’s hold, the lad was ordered to stay on board with the British prize crew and repair the breached hull.

Some days later Iris sailed into New York harbor towing the General Lincoln. When the warships tied up to the wharf, a crowd gathered to see the captive rebels. Greenwood, temporality serving with a British prize crew, was relatively ignored. As some curious townspeople climbed onboard to explore the privateer brig, the ever-opportunistic Greenwood gathered his clothes, took the ship’s valuable quadrant and put them in a makeshift seabag. He then blended into the harborside crowd and casually sauntered away onto the New York pierside streets. Now free, he contacted Ahasuerus Turk, Jr. whom he knew as a fife maker when he was a “fife major” in the army. Turk helped him find a friend of his father, William Hill, a baker and tory. Nevertheless, Greenwood informed Hill of his escape and was allowed to stay in the baker’s house for a few days because he had no money. Hill than suggested that Greenwood volunteer for British merchant service to escape punishment, a proposal he quickly rejected.[10] The tory then contacted another of the erstwhile privateer’s father’s friends, a British army chaplain. The clergyman brought Greenwood to the infamous head of the British navy’s prisons in New York, Commissary General David Sproat.[11] The respected cleric convinced Sproat to include Greenwood in the next prisoner exchange. The cartel landed Greenwood at New London where he sold the quadrant, thus providing funds to return home to Boston. He continued his rather checkered career as a privateer during the final years of the revolution by signing on to two more letters of marque, Aurora and Resolution. Neither were notably successful.

After the war John Greenwood moved to New York City.  The young man had not progressed beyond elementary school but possessed extraordinary mechanical skill. At one point he became a woodturner, producing hickory walking canes. For a time he was a merchant. In 1784 he acquired a rudimentary knowledge of dentistry and commenced to practice the vocation in New York.[12] Greenwood became a self-taught pioneering genius in an undeveloped field and provided impetus for the dental profession that followed. Noted for his mechanical skill and aptitude he became Gen. George Washington’s dentist until the general’s death.[13] During that time, he pioneered the use of a foot-powered dental drill adapted from foot powered looms (variations on this device were in use into the mid-twentieth century).[14] Greenwood formed false teeth from hippopotamus ivory and was an early advocate for using teeth transplanted from one human body to another, replacing their decaying teeth with more healthy teeth. These replacement teeth were purchased from fellow humans who were inclined to sell their anatomical assets.

John Greenwood’s practice flourished in New York where he unreservedly advertised himself in the New York Gazette as “Dentist to His Excellency George Washington.”[15] By 1800 he was considered by many as New York City’s leading dental practitioner. Greenwood’s health declined in 1818 and, about a year later, the multifaceted patriot died from the complications of a stroke at the age of sixty. He wrote a memoir in 1809 that remained unpublished for 113 years, when in the early twentieth century his remarkable career finally came to public notice.[16]


[1]John Greenwood, A Young Patriot in the American Revolution (New York, NY: Westvaco publisher, 1981, reprint of 1922 edition), 41.

[2]Ibid, 42.

[3]Ibid, 43.

[4]Drums and fifes provided marching cadence and timed the movements with which soldiers handled their weapons. They also could relay orders in the form of musical signals. Fifes, somewhat analogous to the navy’s bosun’s whistles or the army’s bugles that were particularly useful because they could be heard over the sounds of battle. They also served in the military band during parades. Often fifers were boys in their early teens and, as they matured, some laid aside their small wind instrument for a musket.

[5]Eric Jay Dolin, Rebels at Sea (New York, NY: Liveright Publishing Company, 2022), 121.

[6]Greenwood, A Young Patriot, 99.

[7]Louis Arthur Norton, Captains Contentious (Columbia, SC: University of South Carolina Press, 2019) 43.

[8]Greenwood, A Young Patriot,106.

[9]Iris was a twenty-eight-gun sixth rate vessel, formerly the American frigate Hancock sailing under then-Commodore John Manley. The ship served the Americans for only sixty-one days. The British captured Hancock in 1777, renamed her Isis but lost her to the French in 1781.

[10]Ibid., 122-123.

[11]David Sproat oversaw the many facilities for holding naval prisoners in New York, among them the hulks in Wallabout Bay including the infamous Jersey.

[12]John Miller, “John Greenwood (1760-1819),” At the time the profession consisted of highly skilled craftsmen with sparse scientific knowledge. They bore little resemblance to today’s highly technical health care specialty. Among the dentists of the era was Paul Revere. John M. Harris founded the world’s firstdental school in Bainbridge, Ohio in 1828 and helped establish dentistryas a health profession. The first dental college in the United States dated to 1840, the Baltimore College of Dental Surgery (now the University of Maryland). The first dental school established as part of a university was Harvard’s School of Dental Medicine founded in 1867.

[13]Greenwood, A Young Patriot, 149-150.

[14]James Anderson Taylor, History of Dentistry (Philadelphia, PA: Lea and Febiger, 1922), 68.

[15]Greenwood, A Young Patriot,150.

[16]The manuscript, handwritten on parchment, was finally published in 1922 by Greenwood’s grandson, Isaac J. Greenwood, through the deVinne Press of New York. One hundred numbered copies were printed under the title The Revolutionary Services of John Greenwood, principally for members of the Greenwood family and friends. It was reprinted in 1981.

One thought on “John Greenwood: Adroit Multi-talented Patriot

  • I enjoyed this article and learned much about John Greenwood’s life as a result. I do wish to point out that there is one omission that I think is significant: Greenwood’s reporting on the Crossing of the Delaware and his participation in and observations about the overnight march and the first Battle of Trenton. Among young Greenwood’s many talents which your article focuses on was another very important one: he was, in spite of his lack of formal education, able to write and express himself very well. His observations on General Washington’s leadership and events of that Christmas night and the surprise attack the next morning on the Hessians are first-rate, highly readable first-hand descriptions of that crucial time. The reprint of the 1922 edition of The Revolutionary Services of John Greenwood by his grandson Isaac Greenwood, as you note, should include John Greenwood’s account of the Crossing and battle at Trenton, although I have only looked at the original 1922 piece. Anyway, thanks for this piece on Greenwood, an important Revolutionary figure.

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